Murray (Woody Allen) is in a bit of a bind. He’s the proprietor of a rare book shop in New York that has been in his family for a couple of generations, but at a time when people aren’t that interested in buying rare books. So he’s folding shop. He lives with his girlfriend, Othella (Tonya Pinkins) and her children, and the loss of income and position is obviously going to impact his life heavily. Also impacted is his longtime employee and good friend, Fioravante (John Turturro), who has worked at the shop since not long after he was caught shoplifting there in his youth. He still has other part-time work as a florist but is losing a source of revenue and doesn’t have much in the way of a reserve to fall back on.

But Murray has stumbled upon a quick and easy way to make a buck, thanks to a passing comment made by his dermatologist, Dr. Parker (Sharon Stone). She’s confided that she and her girlfriend (Sofia Vergara), are in the market for a ménage à trois, leading Murray to conceive the idea of Fioravante filling the male role for a fee, of which Murray would get a cut. And nothing’s easier or more rewarding than the life of a prostitute, right? So yes, that means Fading Gigolo is a film that features Woody Allen playing the pimp of John Turturro’s male prostitute. Sounds kind of crazy, risky and exciting, doesn’t it? Sadly, it’s none of the above.

Turturro, while a highly skilled actor and a capable director, strikes me as not the sharpest of writers. Give Turturro credit; the basic premise of the plot is clever and has a lot of potential, but if, as they say, the devil is in the details, Satan runs wild in Fading Gigolo. Turturro has a hard time putting together all the pieces in such a way that the story feels at all plausible (or at times even possible) or deeply examined. How much that bothers you will probably depend on how much Turturro’s male-imagined, romantic worldview, in which complicated moral questions, self-examination and real-life worries seem to be supplanted by feeling deeply and acting upon those feelings, clicks with you. As for me, I found myself shaking my head repeatedly at the overly sentimental and improbable plot points and cringing repeatedly at the hammy dialogue.

There’s a theoretically moving subplot which involves Avigal (Vanessa Paradis), an ultra-orthodox widow of a regarded Hasidic rabbi and mother of six, who gets involved with Fioravante via Murray, who once sold books to her husband and now goes to her to because she’s an actual nit picker and one of Othella’s kids has lice (this all sounds so lovably quirky as I write about it but alas). Since the death of her husband she’s withdrawn almost completely into the shell of her religion and family, denying herself any and all romantic inclinations. That is until male gigolo Fioravante, in an unlikely turn, reignites them in her and in the process makes himself aware of his own deeply buried loneliness and yearning. The expected cultural complications arise and things are further complicated by the borderline stalker behavior of a neighborhood watch captain (Liev Schreiber) who’s hot for Avigal. His struck me as the kind of behavior that often leads to restraining orders but in this story he’s rewarded for that very behavior because he’s a man of virtue, the kind of guy that feels deeply and then acts upon those feelings.